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February 19, 2026ChemistryEurope0 citationsOpen Access

Introducing TeHyperBTM as an Organocatalyst for (4 + 2)‐Cycloadditions of Michael Acceptors with Allenoates, But‐2‐ynoates or Allenylphosphonates

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MPMagdalena PiringerASAnna ScheucherMHMario Hofer

Key Points

  • The aim is to evaluate the effectiveness of TeHyperBTM as a new organocatalyst for (4 + 2)-cycloadditions.
  • Introduced TeHyperBTM as a chiral isochalcogenourea organocatalyst.
  • Compared reaction performance with its sulfur and selenium analogs HyperBTM and SeHyperBTM.
  • Conducted (4 + 2)-cycloadditions using various Michael acceptors and electron-deficient reactants.
  • TeHyperBTM exhibited increased nucleophilicity and Lewis basicity compared to HyperBTM and SeHyperBTM.
  • It facilitated cycloadditions with less reactive reagents that were ineffective with other catalysts.
  • Improved reaction rates and higher enantioselectivities were observed in the reactions.

Abstract

TeHyperBTM = (2 S ,3 R )‐3‐isopropyl‐2‐phenyl‐3,4‐dihydro‐2 H ‐benzo[4,51,3tellurazolo3,2‐apyrimidine] is introduced as a novel, highly effective, chiral, Lewis basic isochalcogenourea organocatalyst. Compared to its established sulphur‐ and selenium‐based homologues HyperBTM and SeHyperBTM, the increased nucleophilicity and Lewis basicity of TeHyperBTM directly impact its catalytic performance by increasing reaction rates and often also improving enantioselectivities for organocatalytic (4 + 2)‐cycloadditions between Michael acceptors and electron‐deficient allenes or alkynes. Furthermore, less reactive reagents, such as diethyl allenylphosphonate or ethyl but‐2‐ynoate, that were not sufficiently activated by HyperBTM and SeHyperBTM catalysts, underwent smooth (4 + 2)‐cycloadditions with Michael acceptors when using TeHyperBTM as the catalyst, which underscores the high catalytic potential of this novel chiral highly nucleophilic Lewis base.

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Cite This Study

Piringer et al. (2026) studied this question.

synapsesocial.com/papers/6996a768ecb39a600b3ed165https://doi.org/10.1002/ceur.202500443
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